My PhD dissertation - Institut Fresnel

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MS: 412 (5%, M + ), 301 (44%), 173 (100%), 141 (62%).
Ethylbis(1-naphthyl)phosphinite (5): This compound was obtained as a by-product in the
mother liquors, after recrystallization of the tris(1-naphthyl)phosphine (4). The solvent was
evaporated and the crude solid recrystallized from ethanol to afford colorless needles; m.p. 96
- 98 °C; yield: 1.03 g (5.2%).
1 H NMR: δ = 8.4 (m, 2 H), 7.9 (m, 4 H), 7.62 (ddd, J = 6.7, 5.4, 1.3 Hz, 2 H), 7.4
(m, 6 H), 4.05 (qd, J = 9.6, 7.0 Hz, 2 H), 1.35 (t, J = 7.0 Hz) ppm.
13 C NMR: δ = 137.6 (d, J = 21 Hz), 134.8 (d, J = 22 Hz), 133.7 (d, J = 4 Hz),
130.1, 129.9 (d, J = 7 Hz), 129.1 (d, J = 2 Hz), 126.6 (d, J = 2 Hz), 126.2 (d, J = 1
Hz), 125.9 (d, J = 3 Hz), 125.5 (d, J = 3 Hz), 66.8 (d, J = 21 Hz), 17.2 (d,
J = 8 Hz) ppm.
31 P NMR: δ = 104.7 ppm.
MS: 331 (64%, M + + 1), 301 (19%), 173 (49%), 128 (100%).
C22H19OP (330.12) calcd. C 79.98% H 5.80%
Found C 79.97% H 5.88%.
Tris(2-naphthyl)phosphine (6): Prepared from 2-bromonaphthalene (31 g, 0.15 mol);
colorless needles; m.p. 261 - 264 °C (ref. [84] no physical constants reported); yield: 17.2 g
(83%).
1 H NMR: δ = 7.89 (d, J = 8.6, 3 H), 7.82 (t, J = 9.0 Hz, 6 H), 7.73 (d, J = 7.9 Hz,
3 H), 7.5 (m, 9 H) ppm.
13 C NMR: δ = 134.7 (d, J = 11 Hz), 134.5 (d, J = 22 Hz), 133.7, 133.6 (d,
J = 8 Hz), 130.5 (d, J = 18 Hz), 128.5, 128.2 (d, J = 7 Hz), 128.2, 127.0,
126.5 ppm.
31 P NMR: δ = -17.1 ppm.
Tris(3,5-dimethylphenyl)phosphine (7): Prepared from 3,5-dimethyl-iodobenzene (35 g, 0.15
mol) [79] ; colorless needles; m.p. 158 - 160 °C (ref. [85] m.p. 160 - 162 °C); yield: 14.0 g (81%).